Cesium carbonate → HCID 178461250, Verbindung

HRID 81105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81105
Cl[C:2]1[C:7]2[N:8]([CH2:11][C@H:12]3[CH2:17][CH2:16][C@H:15]([CH3:18])[CH2:14][CH2:13]3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([Cl:19])[N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[N:25][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:19][C:4]1[N:3]=[C:2]([C:23]2[CH:24]=[N:25][CH:26]=[C:21]([Cl:20])[CH:22]=2)[C:7]2[N:8]([CH2:11][C@H:12]3[CH2:17][CH2:16][C@H:15]([CH3:18])[CH2:14][CH2:13]3)[CH:9]=[N:10][C:6]=2[CH:5]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 201118775-Chloropyridine-3-boronic acidHCID 178461251HCID 178461251, Verbindung

Produkt 1

HCID 178461250HCID 178461250, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

4,6-dichloro-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (6.8 g, 22.8 mmol), 5-chloropyridine-3-boronic acid (3.95 g, 25.1 mmol), cesium carbonate (22.3 g, 68.4 mmol), and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride (1.67 g, 2.28 mmol) were combined in a vial that had been oven-dried and flushed with nitrogen. Dioxane (73 mL) and water (18 mL) were added, and the vial was sealed and heated to 90° C. for 3 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to afford 6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine. MS ESI calc'd. for C19H20Cl2N4 [M+H]+ 375. found 375.

Aufarbeitung

  1. customhad been oven-dried
  2. customflushed with nitrogen
  3. additionDioxane (73 mL) and water (18 mL) were added
  4. customthe vial was sealed
  5. temperatureThe reaction mixture was cooled to room temperature
  6. additiondiluted with ethyl acetate
  7. washwashed with water
  8. washThe organic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient)

Quellen und Nachweise

ORD-Eintrag
ord-011892b28824416996da338ee84d6553
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846657B2

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